Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/107467
Title: | Petasis adducts of tryptanthrin – synthesis, biological activity evaluation and druglikeness assessment | Authors: | Brandão, Pedro Marques, Carolina Pinto, Eugénia Pineiro, Marta Burke, Anthony J. |
Issue Date: | 2021 | Publisher: | Royal Society of Chemistry | Project: | info:eu-repo/grantAgreement/FCT/POR_CENTRO/PD/BD/128490/2017/PT/Sustainable Asymmetric Catalytic Synthesis of Novel Oxindole Hybrids with Potential Biological Activity info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB/04423/2020/PT/Interdisciplinary Centre of Marine and Environmental Research info:eu-repo/grantAgreement/FCT/REEQ/481/QUI/2006 info:eu-repo/grantAgreement/RECI/QEQ-QFI/0168/2012 info:eu-repo/grantAgreement/CENTRO-07-CT62-FEDER-002012 UIDB/50006/2020 UIDB/00313/2020 |
Serial title, monograph or event: | New Journal of Chemistry | Volume: | 45 | Issue: | 32 | Abstract: | Tryptanthrin is a valuable tetracyclic alkaloid, which displays a wide variety of biological activities. The application of this type of scaffold as a starting material for the discovery of new drug candidates is of major importance in medicinal chemistry. In this work, we report one of the few examples of tryptanthrin-based multicomponent reaction approaches for drug discovery, and the first using the Petasis reaction. The optimized BINOL-catalyzed reaction conditions allowed the synthesis of a library of new tryptanthrin derivatives bearing considerable structural diversity. An asymmetric version was also established, achieving the desired enantiomerically pure derivative with 99% ee and 71% yield. The resulting library was screened against one Gram-positive and one Gram-negative bacteria, two yeasts, and three filamentous and four dermatophyte fungal strains with clinical relevance, with compound 5bea displaying moderate fungicidal activity. | URI: | https://hdl.handle.net/10316/107467 | ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/D1NJ02079J | Rights: | embargoedAccess |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
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File | Description | Size | Format | |
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Brandao2021NewJChem.pdf | 3.98 MB | Adobe PDF | View/Open |
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